Real life is for March: How to take risks on Leap Day (and year-round)

The NBC comedy 30 Rock has a lot of good advice for viewers: Live every week like it’s Shark Week. Always change into a tuxedo after six. But perhaps the most important lesson to be gleaned from Tina Fey’s now-retired series comes from its reimagining of Leap Day. In the world of 30 Rock, Feb. 29 is a joyful, devil-may-care national holiday chockfull of traditions—the most important of which is seizing the extra day that comes every four years to break out of your comfort zone.

“Honey, I’m about to do something really crazy,” the show’s heroine Liz Lemon tells her boyfriend as she contemplates sleeping with a nerdy billionaire in exchange for $20 million. “You should!” he responds, without waiting to hear her explanation. “Nothing that happens on Leap Day counts. Real life is for March.”

On Leap Day, it’s worth taking this attitude to heart. As a famous psychology experiment dating back to 1908 shows, we perform best when we’re working in a state of “optimal anxiety”—a state we can reach by pushing ourselves to take on new challenges and risks. Yet while optimistic, confident types are good (perhaps too good) at taking risks, many others find it difficult to take chances.

“The moment you feel ambiguity, you start thinking about what can go wrong,” Monica Mehta, managing principal at investment firm Seventh Capital and the author of The Entrepreneurial Instinct, tells Quartz. “If we indulge in that behavior, the end result is that we do nothing at all.”

Leap Day William would certainly disapprove. So if you’re looking to free yourself from inertia, here are a few concrete ways to take a leap.

Don’t give drawbacks too much weight.

This advice comes courtesy of Camelia Kuhnen, an associate professor of finance at the University of North Carolina at Chapel Hill’s Kenan-Flagler Business School. Kuhnen has studied the way that people evaluate risks when they invest money. Those who’ve had bad financial experiences in the past, for example, turn out to be overly pessimistic in their assessments of what investments can yield in the future.

The same principle likely applies to people when they’re weighing whether to go back to school or start a new business, according to Kuhnen.

“If you had a bad experience in the past, you become too pessimistic about the future, and this makes you less likely to invest because you do not see the upside of the opportunity that you are faced with,” she tells Quartz in an email.

In order to train yourself to take more risks, Kuhnen recommends carving out time to focus on the advantages of your decisions.

“Just consciously listing or looking for the upside would help a lot,” Kuhnen tells Quartz. “Admitting an upside is possible is a start.”

Sign up for an improv class.

Successful risk-takers tend to exhibit two qualities, according to Mehta: a bias to action and adaptability. Improvisational comedy is a great way to get comfortable with both.

“The reality of this world is all you do is make mistakes,” Mehta tells Quartz. “If you’ve only trained yourself to execute on your plan, you’re unprepared when things go wrong. So learning how to improvise is an enormously important skill that we don’t spend time developing.”

When Mehta herself signed up for an improv class, she found that it was useful to be forced to say yes to new situations rather than find reasons to avoid them. “The basic tenant of improv is that whatever your partner says, you say, ‘Yes, and,’” she explains. “You’re going to accept the conditions that exist and heighten them. So improv is actually a wonderful way to condition yourself to take risks in life.”

When you go to a restaurant, order the first thing you see on the menu.

Risk-averse people have a tendency to obsess over every decision, no matter how small, according to Mehta. That makes it harder to take a chance. “So the idea is to just live with your decision and be comfortable with it,” she says. That could mean sticking with the first outfit you put on in the morning rather than trying out several in front of the mirror, or ordering the first dish you see at a restaurant. With any luck, it will be something that comes with a side of fries.